1. Field of the Invention
The present invention relates to a method for producing acetylene alcohol compounds in a continuous type process using strong basic, heterogeneous anion exchange resins. More specially, the present invention relates to an ethynylation in which acetylene and ketone compounds are condensed in a continuous process in an aprotic solvent in the presence of quaternary ammonium hydroxide anion exchange resins, as represented by the following reaction formula I, thereby producing commercially useful acetylene alcohol compounds at high yields in an environmentally favorable fashion: ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, each is a hydrogen atom, a linear or branched, saturated or unsaturated alkyl containing 1 to 16 carbon atoms, or a linear or branched, saturated or unsaturated phenyl containing 1 to 16 carbon atoms.
2. Description of the Prior Art
Thus far, acetylene alcohol compounds have been prepared through the condensation of ketone and acetylene by the method which was developed by Favorskii. According to Favorskii's method, acetylene is converted into acetylide in the presence of a metal salt capable of deprotonation in liquid ammonia or another suitable solvent, followed by condensing the acetylide with appropriate ketones to provide desired acetylene alcohol compounds. Besides liquid ammonia, ethers are usually used as the solvents. As for the catalysts carrying out the condensation reaction, they comprise metal salts of strong base, e.g, alkaline metal hydroxides, and particularly, potassium hydroxide is usually used.
This method is, however, found to be disadvantageous in several points. First, excess amounts of alkaline metal hydroxide should be used. That is, stoichiometric to excess amounts of metal hydroxides compound to ketones must be used, and this results in a considerable inefficiency in economical and environmental aspects. One of the requirements which a good reaction must meet, is the minimization of undesirable by-products. However, the use of excess amounts of alkaline metal hydroxides induces production of by-products, resulting in a decrease in the production yield of the ultimate objects, acetylene alcohol compounds. Moreover, because the above acetylene alcohol production reaction is reversible, the conversion rate of ketones and the production yield of acetylene alcohols may be decreased during the separation and purification of the product at higher temperature in the presence of a catalyst.
On the basis of the experiment data established thus far, liquid ammonia is used as the most efficient solvent for the reaction in view of the production yield of the desired acetylene alcohol compounds and the conversion rate of ketones. To be used as a solvent, ammonia should be liquified, which requires a very low temperature and thus, a corresponding energy expenditure. In addition, the low temperature imposes a stiff burden on the recovery of the product. Moreover, liquid ammonia is unfavorable to the environment.